This invention relates to the chiral, total synthesis of thienamycin from D-glucose (dextrose).
In its broadest terms, the process proceeds from D-glucose via intermediates I, II, and III and ##STR2## encounters aldehyde IV or acid V, which are known to be useful in the total synthesis of thienamycin (VI). ##STR3## wherein: R is alkyl having 1-6 carbon atoms or the two sulfur atoms may be joined to form a ring comprising R; R.sup.1 is hydrogen or a removable protecting group, such as a triorganosilyl group, (R.degree.).sub.3 Si-- wherein R.degree. values are independently chosen from alkyl having 1-6 carbon atoms, aryl and aralkyl having 6-10 carbon atoms.
The transformations IV.fwdarw.V, IV.fwdarw.VI, and V.fwdarw.VI are known. See for example: U.S. patent application Ser. No. 112,058 (filed Jan. 14, 1980, now abandonded); U.S. Pat. No. 4,234,596 (issued Nov. 18, 1980); and EPO application No. 79202307.1 (filed May 1, 1979; Publication Number No. 007973), which publications and pending application disclose schemes of total synthesis which can be fed by common imtermediates made available by the presently disclosed and claimed process. For the same purpose, the following co-pending, concurrently filed, commonly assigned U.S. patent applications Ser. Nos. 248,174; 248,175; 248,177; and 248,178 are also incorporated by reference.